This invention relates to new chemical compounds. More particularly it relates to new chemical compounds which are of value as antibacterial agents. These new antibacterial agents are bis-esters of methanediol, in which one hydroxy group of the methanediol has been esterified with the carboxy group of a 6-acylaminopenicillanic acid compound, and the other hydroxy group of the methanediol has been esterified with the carboxy group of penicillanic acid 1,1-dioxide.
In addition, this invention relates to the 6'-aminopenicillanoyloxymethyl ester, halomethyl esters, alkylsulfonyloxymethyl esters and arylsulfonyloxymethyl esters of penicillanic acid 1,1-dioxide. The latter compounds are useful intermediates to the antibacterial agents of this invention.
West German Offenlegungsschrift No. 2,824,535, published Dec. 14, 1978, and Iranian Patent No. 19,601, granted July 12, 1978, disclose penicillanic acid 1,1-dioxide, and esters thereof readily hydrolyzable in vivo, as antibacterial agents and as beta-lactamase inhibitors. Penicillanic acid 1,1-dioxide and esters thereof readily hydrolyzable in vivo increase the antibacterial effectiveness of certain penicillin and cephalosporin compounds against certain bacteria.
Belgian Patent No. 764,688, granted Mar. 23, 1971, discloses: (a) certain 6'-acylaminopenicillanoyloxymethyl 6-acylaminopenicillanates; (b) certain 6'-acylaminopenicillanoyloxymethyl 6-aminopenicillanates; (c) 6'-aminopenicillanoyloxymethyl 6-aminopenicillanate; and (d) chloromethyl 6-aminopenicillanate. U.S. Pat. No. 3,850,908 discloses chloromethyl esters of several natural, biosynthetic and semi-synthetic penicillin compounds.
The antibacterial agents of the present invention are efficiently absorbed from the gastrointestinal tract of mammals, and after absorption they are transformed into a 6-acylaminopenicillanic acid and penicillanic acid 1,1-dioxide.